Herbicide

ABSTRACT

Herbicidal mixtures containing an acid anilide in admixture with a pyridazone derivative or a substituted oxazolidine-3,5-dione derivative and a process for controlling the growth of unwanted plants with these mixtures.

I Umted States Patent 1 [111 3,773,492 Fischer 1 Nov. 20, 1973 HERBICIDE75 Inventor: Adolf Fischer, Mutterstadt, [561 References Cited GermanyUNITED STATES PATENTS [73] Assignee: Badische Anilin- & sodajabrik3,535,377 10/1970 Steinbrunn et a]. 71/118 Aktiengesellscha 3,437,6644/1969 Krenzer 71/92 9 Ludwigshafen/Rhineland Rhineland pfalz GermanyPrimary Examiner-Lewls Gotts Assistant ExaminerCatherine L. Mills FllediP 1970 Attorney-Johnston, Root, OKeefie, Keil, Thompson 21 Appl. No.:30,936 & Shurflefi' 57 ABSTRACT [30] Foreign Application Priority Data 61969 G P 19 21 464 3 Herblcldal mixtures containing an acid amlide inad- 2 emany mixture with a pyridazone derivative or a substitutedoxazolidine-3,5-dione derivative and a process for [52] US. Cl 71/92,71/104, 77l1//ll0l58, controlling the growth of unwanted plants withthese 51 lm. Cl. A01n 9/22 [58] Field of Search 71/92, 118 3 Claims, NoDrawings where X denotes thiocyano, halogen (Cl, Br, I), a nitro group,a trifluoromethyl or alkyl radical having one to three carbon atoms, oran alkoxy radical, R denotes an aliphatic radical having one to threecarbon atoms which may be substituted by chlorine, bromine, cyano orthiocyano, R denotes an alkyl radical having one to three carbon atomswhich may be substituted by halogen or R denotes an alkynyl radicalhaving three to five carbon atoms, and n denotes one of the integers 0,

1, 2 and '3, and

b. a pyridazone derivative having the formula where R denotes a phenylradical which may be substituted by methyl or trifluor'omethyl', Rdenotes a cyclohexyl radical, X denotes an amino, acetylamino or methoxyradical,-'a NH-CO-COORgroup, Rdenoting hydrogen or a methyl, ethyl orphenyl radical, and Y denotes chlorine, "bromine, iodine, methyl ormethoxy, or an alkali metal (sodium, potassium) or amine(dimethylethanola'mine, diethylenetriamine, ethanolethyle'nediam'ine,('trimethanol)-methylamine, diethyl- 'ethahola'mine) salt thereof, or

c. an oxadiazolidinedione derivative having the formula where R denotesa M-chlorophenyl, m-trifluoromethylphenyl, 3,4-dichlorophenyl,3-chloro-4-bromophenyl or methylphenyl radical and R denotes a 3,4-dichlo'rophenyl, '4-chlo'ro'phenyl, phenyl, 3-trifluoromethylphenyl,3-isopropylcarbamoyloxyphenyl, 3-butyl- 2 carbamoyloxyphenyl,cyclohexyl, m-etliy lcar bamoyloxyphenyl, m-carboxyisoproplphenyl, ormtert-butylcarbamoyloxyphenyl radical, has a good herbicidal action.

The particular advantage of the herbicides according to the invention isthat they are extremely effective es pecially in dry weather when usedpreemergence against most monoand dicotyledonous weeds. The individualactive ingredients may be mixed with each other in any ratio; it is,however, preferred to use a ratio (by weight) ofa to b or 0 of5 l to l:3.

The herbicides according to the invention may be used as solutions,emulsions, suspensions or dusts. The form of application dependsentirely on the purpose for which the agents are being used; in any caseit should ensure a fine distribution of the active ingredient.

For the preparation ofsolutions to be sprayed direct, the solution inwater is suitable. However, hydrocarbons having boiling points higherthan C, e. g. tetrahydronaphthalene or alkylated naphthalenes, ororganic liquids having boiling points higher than 150 C and having oneor more than one functional group, e. g. the keto group, the ethergroup, the ester group or the amide group, this group or these groupsbeing attached as substituent(s) to a hydrocarbon chain or being acomponent of a heterocyclic ring, may also be used as spray liquids.

Aqueous formulations may be prepared from emulsion concentrates, pastesor wettable powders by adding water. To prepare emulsions theingredients as such or dissolved in a solvent may be homogenized inwater or organic solvents by means of wetting or dispersing agent, e. g.polyethylene oxide adducts. Concentrates which are suitable for dilutionwith water may be prepared from active ingredient, emulsifying ordispersing agent and possibly solvent.

Dusts may be prepared by mixing or grinding the active ingredients witha solid carrier, e. g. kieselguhr,

talc, clay or fertilizers.

The mixtures may be applied per se or in admixture with insecticides,fungicides and fertilizers.

The following comparative experiments illustrate the application of theherbicides according to the invention.

EXAMPLE 1 ent and each mixture being dispersed in 500 liters of waterper hectare:

I chloroacetic acid-N-butyn-( l )-yl-(3)-anilide, 3 and 4 kg perhectare; ll l-cyclohexyl-4-methoxy-5-bromopyridazone-(6),

l and 4 kg per hectare;

lll l-phenyl-4-methoxy-5-bromopyridazone-(6), l

and 4 kg per hectare; l II: 3 1 kg per hectare; l+ Ill: 3 1 kg perhectare.

The results of the experiment after 4 weeks are given in the followingtable.

Active ingredient I II III I+II I+III Application rate in kgJha. 3 4 1 41 4 3+1 3+1 Setaria glauca 90 100 0 50 20 60 90 100 Echinochloacrus-galli 90 100 50 70 70 100 100 100 Paspalum dilatatum 100 100 35 6020 50 100 100 P00 annua 95 100 95 100 50 90 100 100 Lolium perenne.90-100 100 90 100 40 80 100 100 Sinapis arvensis 90 100 80 100 100 90Amaranthus retroflezus 0-10 80 100 70 100 80-90 80 0=no damage;100=comp1ete destruction.

pected from a knowledge of the components of the mixture.

EXAMPLE 2 VI the N,N-dimethylethanolamine salt ofN-[lphenyl-S-bromopyridazon-(6)-yl-(4)]-oxamic An agricultural site issown with Indian coren (Zea acid, 1 and 4 kg per hectare; mays), yellowfoxtail (Setaria glauca), barnyard grass VII the sodium salt of N-[l-phenyI-S- (Echinochloa crus-galli), witchgrass (Panicum bromopyridazon6)-yl-(4)]-oxamic acid, l and 4 capillare), large crabgrass (Digimriasanguinalis), ankg per hectare; nual bluegrass (Poa annua), perennialrygrass (Lolium VIII l-cyclohexl-4-amino-5-bromopyridazone-(6), lperenne), wild mustard (Sinapis arvensis) and redroot and 4 kg perhectare; pigweed (Amaranrhus retroflexus). IXl-cyclohexyl-4,5-dimethylpyridazone-(6), l and 4 The soil prepared inthis manner is then immediately kg per hectare; treated with the statedamounts of the following active I IV: 3 1 kg per hectare; ingredientsand mixtures of them, each active ingredi- I V: 3 1 kg per hectare; emand each mixture being dispersed in 500 liters of 1+ VI: 3 1 kg perhectare; water per hectare: l VII: 3 1 kg per hectare;

Ichloroacetic acid-Nbutyn-(1)-yl-(3)-amilide, 3 and l VIII: 3 1 kg perhectare; 4 kg per hectare; I+ IX: 3 1 kg per hectare. IVl-phenyl-4-amino-5-chloropyridazone-(6), l and The results of theexperiment after 4 weeks are given 4 kg per hectare; in the followingtable.

Active ingredient I IV V VI VII Application rate in kg. /ha a 3 4 1 4 14 1 4 1 4 Zea mays 0 O 0 20 0 30 0 20 0 30 Selaria glauca 90 100 0 10 505-10 40 40 8O Echinochloa crus-gallz 00 100 20 so 30-40 7 50-60 90 100Panicum capillare. 90 90 50 90 90 50-60 90 60 90 Digitaria sanguinalis.100 100 10 so 30 7 20 50 40 80 P00 annua 95 0 80 100 50-00 90 100 1 100Lolium perenne" 90-100 100 90 50 90 60 100 70 100 Sinapis arvensis 10 5100 90 100 100 100 Amaranthus retroflezus 0-10 20 80 100 90 100 70 90 90100 VII IX I+1V I+V I+VI I-l-VII I+VIII I+IX Application rate in KgJha.l 4 1 4 3+1 3+1 3+1 3+1 3+1 3+1 Zeamays H 0 20 0 20 0 0 0 0 0 0 Setarz'aglauca 10 40 50 70 00 100 00-100 100 100 100 Echinochloa crus-gallL. 1040 50 70 100 100 100 100 100 100 Panicum capillare 20 e0 30 50 100 100100 100 100 100 Digitan'a sunguinalis. 10 50 20 40 100 100 100 100 100100 Foo annua 70 90 70 90 100 100 100 100 100 100 Lolium perenne 70 9070 90 100 100 100 100 100 100 Sinapis arvensis so 100 90 100 00 100 100100 90 100 Amaranthus retr0fleIus 70 90 so 100 00 90-100 70-80 90-10070-80 80-90 0 no action; 100 complete destruction. Norm-These resultsshow that the herbicides according to the invention have not only asurprising action on weeds but also in particular a selective actionwhich could not be expected from a knowledge of the components of themixture.

EXAMPLE 3 An agricultural site is sown with soya bean (Glycine hispida),yellow foxtail (Setaria glauca), barnyard grass (Echinochloacrus-galli), large crab-grass (Digitaria sanguinalis), perennialryegrass (Lolium perenne), wild mustard (Sinapis arvensis) and redrootpigweed (Amaranthus relroflexus). The soil prepared in this manner isthen immediately treated with the stated amounts of the actveingredients and mixture of them, each active ingredient and the mixturebeing dispersed in 500 liters of water per hectare:

I chloroacetic acid-N-butyn-(l)yl-(3)-anilide, 3 and 4 kg per hectare;

X l-phenyl-4,5-dimethoxypyridazone-(6), 1 and 4 kg per hectare;

l+ X: 3 1 kg per hectare.

The results of the experiment after 4 weeks are given 'in the followingtable:

Active ingredient O no damage 100 complete destruction The results showthat the herbicides according to the invention have not only asurprising action on weeds but also in particular a selective actionwhich could not be expected froma knowledge of the components of themixture.

EXAMPLE 4 An agricultural site is sown with cotton (Gossypiumherbaceum), barnyard grass (Echinochloa crus-galli), large crabgrass(Digitaria sanguinalis), annual bluegrass (Poa annua), 1 perennialryegrass (Lolium perenne), redroot pigweed (Amaranthus retroflexus) andwild radish (Raphanus raphanistrum The soil prepared in this manner isthen immediately treated with the stated amounts of the following activeingredients and mixture of them, each active ingredient and the mixturebeing disposed in 500 liters of water per hectare:

I chloroacetic acid-N-butyn-( l )-yl-(3)-anilide, 3 and 4 kg perhectare;

XI l-m-trifluoromethylphenyl-4-methoxy-5- chloropyridazone-(G), l and 4kg per hectare;

1+ X1: 3 1 kg per hectare.

The results of the experiment after 4 weeks are given in the followingtable:

Active ingredient 0 no damage 100 complete destruction These resultsshow that the herbicides according to the invention have not only asurprising action on weeds but also in particular a selective actionwhich could not be expected from a knowledge of the components of themixture.

EXAMPLE 5 In a greenhouse, sandy soil is filled into pots and sown withthe seeds of Indian corn (Zea mays), cotton (Gossypium herbaceum),yellow foxtail (Setaria glauca), large crabgrass (Digitariasnaguinalis), barnyard grass (Echinochloa crus-galli), annual bluegrass(Poa annua), redroot pigweed (Amaranlhus retroflexus) and wild mustard(Sinapis arvensis). The soil prepared in this manner is then immediatelytreated with the stated amounts of the following active ingredients andmixture of them, each active ingredient and the mixture being dispersedin 500 liters of water per hectare:

l chloroacetic acid-N-butyn-( l )-yl-(3)-anilide; 3 and 4 kg perhectare;

XII N-[ l-phenyl-S-bromopyridazon-(6)-yl-(4 oxamic acid phenyl ester, 1and 4 kg per hectare;

l XII: 3 1 kg per hectare.

The results of the experiment after 4 weeks are given in the followingtable:

Active ingredient l Xll I Xll Application rate in kg/ha 3 4 l 4 3 I Zeamays 0 0 0 20 0 Gassypium herbaceum O O 0 20 0 Selaria glauca 90 I00 30I00 Digilaria sanguinalis 100 I00 40 70 I00 Echinochlaa crus-galli I0030 60 I00 Poa annua 70 I00 100 Amaranthus rerroflexus 0-10 20 80 I0080-90 Sinapis arvensis l0 15 80-90 100 90-100 0 no damage 100 completedestruction.

These results show that the herbicides according to the invention havenot only a surprising action on weeds but also in particular a selectiveaction which could not be expected from a knowledge of the components ofthe mixture.

EXAMPLE 6 An agricultural site is sown with cotton (Gossypiumherbaceum), Indian corn (Zea mays), yellow foxtail (Setaria glauca),large crabgrass (Digitaria sanguinalis), barnyard grass (Echinochloacrus-galli), slender foxtail (Alopecurus myosuroides), annual bluegrass(Poa annua), perennial ryegrass (Lolium perenne), field pennycress(Thlaspi arvense), redroot pigweed (Amaranthus retroflexus), wildmustard (Sinapis arvensis) and wild radish (Raphanus raphanistrum). Thesoil prepared in this manner is then immediately treated with the statedamounts of the following active ingredients and mixture of them, eachactive ingredient and the mixture being dispersed in 500 liters of waterper hectare:

l chloroacetic acid-N-butyn-( l )-yl-(3)-anilide, 3 and 4 kg perhectare;

XIII 4-( 3,4-dichlorophenyl)-2-methyl-l ,2,4-

oxadiazolidine-3,5-dione, 1 and 4 kg per hectare;

I XIII: 3 1 kg per hectare.

The results of the experiment after 4 weeks are given in the followingtable:

Active ingredient I X111 1 XIII Application rate 176 kg/ha 3 4 l 4 3 1caii'a' iim he rbac eum 0 0 0 10-20 0 Zea mays 0 0 0 10-20 0 Setariaglauca 90 100 20-30 70 I00 7 8 g i x 83 :33 60 95 I (Setaria glauca),large crabgrass (Digitaria c inoc oa crus-ga i 40 70 100 Alopecurusrnyosuroides 70 80 70 WHO) m0 sangumalzs), bamyard grass (Echm ochloaCrus-gallz), Poa annua 95 100 20-30 90 100 slender foxta1l (alopecurusmyosurozdes), annual blue- :3222: 23 8 :8 33 :83 grass (Poa annua),perennial ryegrass (Lolium Amaranthus retroflexus O-IO 20 100 100 100 pwild Oat (Avena f fi pennycress i arvenslils 8 2 33 :33 3g (Thlaspiarvense), redroot pigweed (Amaranthus 32: 2; amsuum retroflexus), wildmustard (Sinapis arvensis) and wild 100 complete destruction radish(Raphanus raphanisrrum). The soil prepared in this manner is thenimmediately treated with the stated These results show that theherbicides according to amounts of the following active ingredients andmixthe invention have not only a surprising action on tures of them,each active ingredient and each mixture weeds but also in particular aselective action which being di er ed in 500 liters of water perhectare: could not be expected froma knowledge of the compo- Ichloroacetic acid-N-butyn-( l )-yl-(3)-anilide, 3 and nents of themixture. 4 kg per hectare;

XVI 2- 3-chloro-4-bromo hen l -4-meth l-1,2,4- EXAMPLE7 p y) yoxad1azol1dme-3,S-drone, l and 4 kg per hectare; An agricultural site issown with soya bean (Glycine X 2- 3,4- 4- 2 i p Indian Corn m y-v),green fOXtail (Sewn.a oxadiazolidine-3,S-dione, l and 4 kg per hectare;viridis), large crabgrass (Digitaria sanguinalis), barn- XVIII2-(4-chlorophenyl)-4-methyl-1,2,4 yard grass (Echinochloa crus-galli),slender foxtail oxadiazolidine-S,S-dione, 1 and 4 kg per hectare;(Alopercurus myosuroides), annual bluegrass (Poa I+ XVI; 3 1 kg perhectare; annua), perennial ryegrass (Lolium perenne), field pen- I+XVII; 3 1 k per h nycress (Thlaspi arvense), redroot pigweed I XVIII; 31 k per b a (Amflmnlhus fl Wild mustard i pi The results of theexperiment are given in the followarvensis) and wild radish (Raphanusraphanistrum). i table; The soil prepared in this manner is thenimmediately WWW w treated with the stated amounts of the followingactive ingredients and mixtures of them, each active ingredient and eachmixture being dispersed in 500 liters of Actlveingredient water perhectare: 1 XVI XVII l chloroacetic ac1d-N-butyn-( l )-yl-(3)-an1l1de, 3and Application ratein kgJha" 3 4 l 4 1 4 4 kg per hectare; XIV 2-(m-butylcarbamoylphenyl)-4-methyll ,2,4- gossypiam herbacemn 0 0 0 10 010 oxadiazolidine-3,S-dione, l and 4 kg per hectare; jg gggf 13g 188 32g 2g 38 igz' ria sanguin is O 0 7 0 XV 2 f lsoPrPpyicarbzfmoylphenyi) 4methyl Echinochalo crus-galli 00 100 30 35 70l,2,4-oxadiazol1d1nel3,5-d1one, l and 4 kg per Alopecurusmyosuroides 708O 2O 50 50 80 h t Poaa1mua .1 95 100 20 35 90 are, fiazimij erenne 0010 12 50 g5 g0 00 vcna a ua 1 7 0 0 0 100 I XIV' 3 l ke per hectareThlaspiaruense 50 7 -80 100 90 100 1+ XV: 3 1 kg per hectare.Apzaranthusrrtrofiexus 0-10 20 00-100 100 00-100 100 The results of theexperiment are given in the follow- 40 figgfjggg'fggm $8 $3 28 38388 188$8 ia twP v Active ingredient I XIV xv I+XIV I+XV Application rate inkg./ha 3 4 1 4 1 4 3+1 3+1 Glycine hispida 0 0 0 40 0 50 0 0 Zea Ma s...0 1 0 0 40 0 2O 0 0 semi-1a viridz's- 90 100 20 00 30 70 100 100Diaitaria aanguz 100 100 30 70 40 100 100 Echinochloa crua-gallL 100 4050 100 100 Alopecurus myosuroides 70 80 20 80 30 90 90 100 95 100 10 7020 95 100 100 00-100 100 10 10 20 00 100 100 50 70 so 100 00 100 100 1000-10 20 so 00 100 100 90-100 100 Sma is arvemis... 10 15 90 100 100 100100 100 Rap anua raphanis 20 40 90 100 100 100 100 100 0:110 damage;100=complete destruction.

These results show that the herbicides according to 60 Active ingredientthe invention have not only a surprising action on V weeds but also inparticular a selective action which X In H'XVI H'XVH I+XVHI Applicationrate in kg./ could not be expected from a knowledge of the compo ha n 43+1 3+1 3+1 nents of the mixture.

Gossypium hcrbaccum 0 3O 0 0 0 EXAMPLE 8 65 Zeamays 0 30 0 0 0 fftatriaglaucaut l 50 J0 100 100 igz' aria sanqui'na 1s 20 70 100 100 100 Anagricultural site 18 sown with cotton (Gossypzurrz mhmochloacmwallt" 1060 100 100 100 herbaceum), Indian corn (Zea mays), yellow foxta|lAlopccurusilLI/OsuroideL 30 70 00 100 100 Active ingredient XVIII I+XVII+XVII I+XVIII Application rate in kg./

I ha 1 4 3+1 3+1 3+1 'Pifidhnim; 100 100 i730 I Lolium perenn 100 10090-100 100 Avena fatua. 100 80 80-90 100 Thlaspi arwmse 80 100 100 100100 Amaranthus retr0flerus. 100 100 100 100 100 Sinapis arvemis 00 10090 100 100 Raphzmus raphanistrum. 90 100 100 100 100 0=n0 damage;100=c0mplete destruction.

chloroacetic acid-N-3-methylbutyn-( l )-yl-(3 anilide, and

chloroacetic acid-N-3-methylbutyn-( l )-yl-( 3 )-mmethylanilide inadmixture with the pyridazone compounds named in Examples 1 to or withthe oxazolidinedione compounds named in Examples 6 to 8.

We claim: I l. A herbicide composition consisting essentially of aherbicidally effective amount of a. an anilide having the formulawherein R denotes CH Cl and R denotes isopropyl or butynyl and (b)2-(3,4-dichlorophenyl)-4-methyll,2,4-oxadiazolidine-3,S-dione, theweight ratio of a to b being in the range of 1:1 to 1:3.

2. A herbicide composition consisting essentially of a herbicidallyeffective amount of a mixture of chloroacetic acid-N-butyn-( l)-yl-(3)-anilide, and (b) 2-(3,4- dichlorophenyl )-4-methyll,2,4-oXadiazolidine-3 ,5- dione in a ratio of 1:1 to 1:37

3. A process for controlling growth of unwanted plants which comprisesapplying to the plants or to the soil in which the growth of the plantsis to be prevented a herbicidally effective amount of a herbicidecomposition consisting essentially of a mixture of (a) chloroaceticacid-N-butyn-( l )-yl-(3)-anilide, and (b) 2-(3,4-

dichlorophenyl)-4-methyll ,2,4-oxadiazolidine-3 ,5-

dione in a weight ratio of 1:1 to 1:3.

2. A herbicide composition consisting essentially of a herbicidallyeffective amount of a mixture of chloroaceticacid-N-butyn-(1)-yl-(3)-anilide, and (b)2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione in aratio of 1:1 to 1:3.
 3. A process for controlling growth of unwantedplants which comprises applying to the plants or to the soil in whichthe growth of the plants is to be prevented a herbicidally effectiveamount of a herbicide composition consisting essentially of a mixture of(a) chloroacetic acid-N-butyn-(1)-yl-(3)-anilide, and (b)2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione in aweight ratio of 1:1 to 1:3.